Molecular chirality study has become one of the most important frontiers in exploratory organic synthetic research. The activities of many pharmaceuticals, fragrances, food additives, and agrochemicals are often associated with their chiral configuration. A compound of a wrong enantiomeric form may lack desirable biological, physical or chemical properties. In the fragrance industry, there is an ongoing need to provide new chemicals including new chiral compounds to give perfumers and other persons the ability to create new fragrances for perfumes, colognes and personal care products. However, identifying a chiral center and developing a cost-effective process to synthesize enantiomers and/or targeted racemic compounds pose difficult challenges, let alone discovering an active form is unpredictable as such effort may often not lead to a desirable enantiomer that exhibits a stronger fragrance effect than the others and/or its racemic mixture.
The present invention concerns novel optically active ester compounds represented by Formulas I set forth below:
wherein * indicates a chiral center.
The racemic compounds of Formula I are known in the art. U.S. Pat. Nos. 6,774,260 and 6,919,477, both belonging to the present Applicants, disclose the compound ethyl 1-(3,3-dimethyl-1′-cyclohexyl)ethyl malonate with absolute configuration of “R” or “S” at carbon 1 position. However, the additional chiral center at carbon 1′ position has never been taught or suggested in the art. The present invention discloses in particular an enantiomer involving the newly identified chiral center and its related racemic compounds as well as their unexpected advantageous use in perfumery.